(2,5-Difluorophenyl)boronic acid → HCID 71539215, compound

HRID 1915844Notes

Reaction equation

Br[C:2]1[S:3][C:4]([NH:32]C(OC(C)(C)C)=O)=[C:5]([C:7]([NH:9][C:10]2[CH:11]=[N:12][N:13]([CH3:31])[C:14]=2[N:15]2[CH2:21][C:20]([F:23])([F:22])[CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)=[O:8])[N:6]=1.[F:40][C:41]1[CH:46]=[CH:45][C:44]([F:47])=[CH:43][C:42]=1B(O)O>>[NH2:32][C:4]1[S:3][C:2]([C:45]2[CH:46]=[C:41]([F:40])[CH:42]=[CH:43][C:44]=2[F:47])=[N:6][C:5]=1[C:7]([NH:9][C:10]1[CH:11]=[N:12][N:13]([CH3:31])[C:14]=1[N:15]1[CH2:21][C:20]([F:23])([F:22])[CH2:19][NH:18][CH2:17][CH2:16]1)=[O:8]

Participants

Reactant 2

HCID 2734335(2,5-Difluorophenyl)boronic acid

HCID 86680063HCID 86680063, compound

Product 1

HCID 71539215HCID 71539215, compoundYield 28%

Procedure

Following the procedure for Example 105, reacting tert-butyl 4-(4-(2-bromo-5-(tert-butoxycarbonylamino)thiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-6,6-difluoro-1,4-diazepane-1-carboxylate and 2,5-difluorophenylboronic acid gave 106 as a beige solid (57 mg, 28% over two steps). 1H NMR (400 MHz, CDCl3) δ 8.90 (s, 1H), 7.88-7.81 (m, 2H), 7.18-7.10 (m, 1H), 7.06-6.99 (m, 1H), 6.16 (s, 2H), 3.78 (s, 3H), 3.70-3.56 (m, 2H), 3.44 (t, J=14.0 Hz, 2H), 3.35 (t, J=5.5 Hz, 2H), 3.11-3.05 (m, 2H), 1.95 (s, 1H). LCMS (ES+) m/z 470 (M+1).

Sources & evidence

ORD record: ord-a45d63bc8bf048978a1acab6b0786e71
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614206B2

Reaction notes

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