(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 → Methyl(S)-2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5'-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

HRID 1482011Notes

Reaction equation

HRID 1482011 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C@H:12]([CH2:14][CH:15]=[CH2:16])[CH3:13])=[C:6](B(O)O)[CH:7]=1.[CH2:17]([O:20][C:21]1([CH3:54])[CH2:26][CH2:25][N:24]([C:27]2[N:32]3[CH:33]=[C:34]([C:36]4[CH:41]=[CH:40][CH:39]=[C:38](Br)[CH:37]=4)[N:35]=[C:31]3[CH:30]=[C:29]([CH3:43])[C:28]=2[C@H:44]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])[C:45]([O:47][CH3:48])=[O:46])[CH2:23][CH2:22]1)[CH:18]=[CH2:19].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>>[CH2:17]([O:20][C:21]1([CH3:54])[CH2:22][CH2:23][N:24]([C:27]2[N:32]3[CH:33]=[C:34]([C:36]4[CH:37]=[C:38]([C:6]5[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=5[O:11][C@H:12]([CH2:14][CH:15]=[CH2:16])[CH3:13])[CH:39]=[CH:40][CH:41]=4)[N:35]=[C:31]3[CH:30]=[C:29]([CH3:43])[C:28]=2[C@H:44]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])[C:45]([O:47][CH3:48])=[O:46])[CH2:25][CH2:26]1)[CH:18]=[CH2:19]

Participants

4

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)acetateHCID 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)acetateHCID 123488148(S)-(5-Fluoro-2-(pent-4-en-2-yloxy)phenyl)boronic acid

Product 1

HCID 118308843Methyl(S)-2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5'-fluoro-2'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetateYield 82%

Procedure

Prepared in 82% yield from (S)-(5-fluoro-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. LCMS (ESI, M+1): 684.4.

Sources & evidence

ORD record
ord-cd41c63725db4244a3bdfbc1291708fe
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

Loading…