(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-(2'-fluoro-6'-hydroxy-4'-methyl-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate

HRID 1482041Notes

Reaction equation

HRID 1482041 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([OH:9])[C:3]=1B(O)O.[CH2:13]([O:16][C:17]1([CH3:50])[CH2:22][CH2:21][N:20]([C:23]2[N:28]3[CH:29]=[C:30]([C:32]4[CH:37]=[CH:36][CH:35]=[C:34](Br)[CH:33]=4)[N:31]=[C:27]3[CH:26]=[C:25]([CH3:39])[C:24]=2[C@H:40]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[C:41]([O:43][CH3:44])=[O:42])[CH2:19][CH2:18]1)[CH:14]=[CH2:15].C(OC1(C)CCN(C2N3C=C(C4C=C(C5C=C(C)C=CC=5O)C=CC=4)N=C3C=C(C)C=2[C@H](OC(C)(C)C)C(OC)=O)CC1)C=C>>[CH2:13]([O:16][C:17]1([CH3:50])[CH2:18][CH2:19][N:20]([C:23]2[N:28]3[CH:29]=[C:30]([C:32]4[CH:33]=[C:34]([C:3]5[C:4]([OH:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=5[F:1])[CH:35]=[CH:36][CH:37]=4)[N:31]=[C:27]3[CH:26]=[C:25]([CH3:39])[C:24]=2[C@H:40]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[C:41]([O:43][CH3:44])=[O:42])[CH2:21][CH2:22]1)[CH:14]=[CH2:15]

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 118308900(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2'-hydroxy-5'-methyl-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetateHCID 1317366642-Fluoro-6-hydroxy-4-methylphenylboronic acid

Product 1

HCID 118308851(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2'-fluoro-6'-hydroxy-4'-methyl-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetateYield 100%

Procedure

Prepared in 100% yield from (2-fluoro-6-hydroxy-4-methylphenyl)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 of (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2′-hydroxy-5′-methyl-[1,1′-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate. LCMS (ESI, M+1): 630.3.

Sources & evidence

ORD record
ord-50b64751f2ba4fe1a8f449aa9f9950e5
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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