(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(4',5'-difluoro-2'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)-7,8-dimethylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate → (S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-7,8-dimethyl-2-(2'-((S)-pent-4-en-2-yloxy)-5'-(trifluoromethoxy)-[1,1'-biphenyl]-3-yl)imidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate

HRID 1482088Notes

Reaction equation

CN1CC(=O)OB([C:11]2[CH:16]=[C:15]([O:17][C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:13][C:12]=2[O:22][C@H:23]([CH2:25][CH:26]=[CH2:27])[CH3:24])OC(=O)C1.[CH2:29]([O:32][C:33]1([CH3:67])[CH2:38][CH2:37][N:36]([C:39]2[N:44]3[CH:45]=[C:46]([C:48]4[CH:53]=[CH:52][CH:51]=[C:50](Br)[CH:49]=4)[N:47]=[C:43]3[C:42]([CH3:55])=[C:41]([CH3:56])[C:40]=2[C@H:57]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])[C:58]([O:60][CH3:61])=[O:59])[CH2:35][CH2:34]1)[CH:30]=[CH2:31].C(OC1(C)CCN(C2N3C=C(C4C=C(C5C=C(F)C(F)=CC=5O[C@H](CC=C)C)C=CC=4)N=C3C(C)=C(C)C=2[C@H](OC(C)(C)C)C(OC)=O)CC1)C=C>>[CH2:29]([O:32][C:33]1([CH3:67])[CH2:34][CH2:35][N:36]([C:39]2[N:44]3[CH:45]=[C:46]([C:48]4[CH:49]=[C:50]([C:11]5[CH:16]=[C:15]([O:17][C:18]([F:19])([F:20])[F:21])[CH:14]=[CH:13][C:12]=5[O:22][C@H:23]([CH2:25][CH:26]=[CH2:27])[CH3:24])[CH:51]=[CH:52][CH:53]=4)[N:47]=[C:43]3[C:42]([CH3:55])=[C:41]([CH3:56])[C:40]=2[C@H:57]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])[C:58]([O:60][CH3:61])=[O:59])[CH2:37][CH2:38]1)[CH:30]=[CH2:31]

Participants

Reactant 3

HCID 118308836(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(4',5'-difluoro-2'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)-7,8-dimethylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate

HCID 118308864(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7,8-dimethylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate

HCID 131736669(S)-6-Methyl-2-(2-(pent-4-en-2-yloxy)-5-(trifluoromethoxy)phenyl)-1,3,6,2-dioxazaborocane-4,8-dione

Product 1

HCID 118308884(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-7,8-dimethyl-2-(2'-((S)-pent-4-en-2-yloxy)-5'-(trifluoromethoxy)-[1,1'-biphenyl]-3-yl)imidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetateYield 92%

Procedure

Prepared from (S)-6-methyl-2-(2-(pent-4-en-2-yloxy)-5-(trifluoromethoxy)phenyl)-1,3,6,2-dioxazaborocane-4,8-dione and (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7,8-dimethylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate in 92% yield following the same procedure as (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(4′,5′-difluoro-2′-((S)-pent-4-en-2-yloxy)-[1,1′-biphenyl]-3-yl)-7,8-dimethylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate. LCMS (ESI, M+1): 746.85.

Sources & evidence

ORD record: ord-2e9bfb2d14e9449489c1845bdc8e0237
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409922B2

Reaction notes

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