(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate → (S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(4',5'-dimethyl-2'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate

HRID 1482029Notes

Reaction equation

[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](B(O)O)=[C:4]([O:12][C@H:13]([CH2:15][CH:16]=[CH2:17])[CH3:14])[CH:3]=1.[CH2:18]([O:21][C:22]1([CH3:55])[CH2:27][CH2:26][N:25]([C:28]2[N:33]3[CH:34]=[C:35]([C:37]4[CH:42]=[CH:41][CH:40]=[C:39](Br)[CH:38]=4)[N:36]=[C:32]3[CH:31]=[C:30]([CH3:44])[C:29]=2[C@H:45]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])[C:46]([O:48][CH3:49])=[O:47])[CH2:24][CH2:23]1)[CH:19]=[CH2:20].C(OC1(C)CCN(C2N3C=C(C4C=C(C5C=CC(F)=CC=5O[C@H](CC=C)C)C=CC=4)N=C3C=C(C)C=2[C@H](OC(C)(C)C)C(OC)=O)CC1)C=C>>[CH2:18]([O:21][C:22]1([CH3:55])[CH2:23][CH2:24][N:25]([C:28]2[N:33]3[CH:34]=[C:35]([C:37]4[CH:38]=[C:39]([C:5]5[CH:6]=[C:7]([CH3:8])[C:2]([CH3:1])=[CH:3][C:4]=5[O:12][C@H:13]([CH2:15][CH:16]=[CH2:17])[CH3:14])[CH:40]=[CH:41][CH:42]=4)[N:36]=[C:32]3[CH:31]=[C:30]([CH3:44])[C:29]=2[C@H:45]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])[C:46]([O:48][CH3:49])=[O:47])[CH2:26][CH2:27]1)[CH:19]=[CH2:20]

Participants

Reactant 3

HCID 118308811(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate

HCID 118308907(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(4'-fluoro-2'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate

HCID 123664321(S)-(4,5-Dimethyl-2-(pent-4-en-2-yloxy)phenyl)boronic acid

Product 1

HCID 118308926(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(4',5'-dimethyl-2'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetateYield 77%

Procedure

Prepared in 77% yield from (S)-(4,5-dimethyl-2-(pent-4-en-2-yloxy)phenyl)boronic acid and (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate following the procedure for (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(4′-fluoro-2′-((S)-pent-4-en-2-yloxy)-[1,1′-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate. 1H NMR (400 MHz, CDCl3) δ 8.03 (d, J=11.5 Hz, 2H), 7.92-7.87 (m, 1H), 7.58-7.52 (m, 1H), 7.43 (s, 1H), 7.32 (s, 1H), 7.22 (s, 1H), 6.81 (s, 1H), 6.11-5.99 (m, 2H), 5.82-5.68 (m, 1H), 5.48-5.38 (m, 1H), 5.10-4.94 (m, 3H), 4.27-4.19 (m, 1H), 4.07-3.92 (m, J=5.0 Hz, 3H), 3.87-3.76 (m, 1H), 3.69 (s, 3H), 3.06-2.97 (m, 1H), 2.79-2.68 (m, 1H), 2.47 (s, 3H), 2.42-2.34 (m, 1H), 2.30 (s, 3H), 2.26 (s, 3H), 2.25-2.18 (m, 1H), 2.02-1.95 (m, 2H), 1.86-1.75 (m, 2H), 1.29 (s, 3H), 1.27 (s, 9H), 1.16 (d, J=6.3 Hz, 3H); LCMS (ESI, M+1): 694.35.

Sources & evidence

ORD record: ord-bfed6de8365a4770a0640536dab41f43
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409922B2

Reaction notes

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