3,5-Difluoro-4-(tributylstannyl)pyridine → HCID 74983259, compound

HRID 1915941Notes

Reaction equation

C(OC([NH:8][C:9]1[S:13][C:12](Br)=[N:11][C:10]=1[C:15]([NH:17][C:18]1[CH:19]=[N:20][N:21]([CH3:40])[C:22]=1[N:23]1[CH2:29][C:28]([F:31])([F:30])[CH2:27][CH:26]([NH:32]C(=O)OC(C)(C)C)[CH2:25][CH2:24]1)=[O:16])=O)(C)(C)C.[F:41][C:42]1[CH:43]=[N:44][CH:45]=[C:46]([F:61])[C:47]=1[Sn](CCCC)(CCCC)CCCC>>[NH2:8][C:9]1[S:13][C:12]([C:47]2[C:46]([F:61])=[CH:45][N:44]=[CH:43][C:42]=2[F:41])=[N:11][C:10]=1[C:15]([NH:17][C:18]1[CH:19]=[N:20][N:21]([CH3:40])[C:22]=1[N:23]1[CH2:24][CH2:25][CH:26]([NH2:32])[CH2:27][C:28]([F:30])([F:31])[CH2:29]1)=[O:16]

Participants

Reactant 2

HCID 164271233,5-Difluoro-4-(tributylstannyl)pyridine

HCID 86680140tert-butyl 1-(4-(5-(tert-butoxycarbonyl-amino)-2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-6,6-difluoroazepan-4-ylcarbamate

Product 1

HCID 74983259HCID 74983259, compoundYield 43%

Procedure

Following the procedure for Example 422 starting from tert-butyl 1-(4-(5-(tert-butoxycarbonyl-amino)-2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-6,6-difluoroazepan-4-ylcarbamate and 3,5-difluoro-4-(tributylstannyl)pyridine gave 438 as a white solid (68 mg, 43% over two steps). 1H NMR (400 MHz, d6-DMSO) δ 8.83 (s, 1H), 8.67 (s, 2H), 7.78 (s, 2H), 7.61-7.56 (m, 1H), 3.79-3.56 (m, 4H), 3.46-3.33 (m, 1H), 3.37-3.16 (m, 2H), 3.16-3.06 (m, 1H), 2.35-2.08 (m, 2H), 1.91-1.78 (m, 1H), 1.81-1.60 (m, 3H). LCMS (ES+) m/z 485 (M+1)

Sources & evidence

ORD record: ord-ea08340bae7b466497feafb61e2bbf08
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614206B2

Reaction notes

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