3,5-Difluoro-4-(tributylstannyl)pyridine → HCID 74983261, compound

HRID 1915942Notes

Reaction equation

HRID 1915942 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]([CH3:41])[C:22]=1[N:23]1[CH2:29][C:28]([O:31][CH3:32])([CH3:30])[CH2:27][CH:26]([NH:33]C(=O)OC(C)(C)C)[CH2:25][CH2:24]1)=[O:16])=O)(C)(C)C.[F:42][C:43]1[CH:44]=[N:45][CH:46]=[C:47]([F:62])[C:48]=1[Sn](CCCC)(CCCC)CCCC>>[NH2:8][C:9]1[S:13][C:12]([C:48]2[C:47]([F:62])=[CH:46][N:45]=[CH:44][C:43]=2[F:42])=[N:11][C:10]=1[C:15]([NH:17][C:18]1[CH:19]=[N:20][N:21]([CH3:41])[C:22]=1[N:23]1[CH2:24][CH2:25][CH:26]([NH2:33])[CH2:27][C:28]([O:31][CH3:32])([CH3:30])[CH2:29]1)=[O:16]

Participants

3

Reactant 2

HCID 164271233,5-Difluoro-4-(tributylstannyl)pyridineHCID 89456933HCID 89456933, compound

Product 1

HCID 74983261HCID 74983261, compound

Procedure

Following the procedure for Example 422 starting from tert-butyl 1-(4-(5-(tert-butoxy-carbonyl-amino)-2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-6-methoxy-6-methylazepan-4-ylcarbamate and 3,5-difluoro-4-(tributylstannyl)pyridine gave 440 as the monoformate salt as a white solid (67 mg, 43% over two steps). 1H NMR (400 MHz, d6-DMSO) δ 8.84 (s, 1H), 8.70 (s, 2H), 8.45 (s, 1H), 7.82 (s, 2H), 7.70 (s, 1H), 3.68 (s, 3H), 3.52 (t, J=11.2 Hz, 2H), 3.36-3.19 (m, 3H), 3.13-3.04 (m, 1H), 3.04 (s, 3H), 2.98 (d, J=14.4 Hz, 1H), 2.18 (d, J=14.2 Hz, 1H), 2.12-1.98 (m, 1H), 1.85-1.75 (m, 1H), 1.68-1.57 (m, 1H), 1.03 (s, 3H). LCMS (ES+) m/z 493 (M+1)

Sources & evidence

ORD record
ord-18cb8cf9c8a74e25bc80511ba4a6c9d2
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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