5-bromo-1H-pyrrolo[2,3-b]pyridine → HCID 90313722, compound

HRID 1523907Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[F:11][C:12]1[CH:13]=[C:14]([C:27]2[C:28]([S:33]([NH:36][CH2:37][CH2:38][OH:39])(=[O:35])=[O:34])=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:15]=[CH:16][C:17]=1B1OC(C)(C)C(C)(C)O1>>[F:11][C:12]1[CH:13]=[C:14]([C:27]2[C:28]([S:33]([NH:36][CH2:37][CH2:38][OH:39])(=[O:34])=[O:35])=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:15]=[CH:16][C:17]=1[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

Reactant 2

HCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

HCID 90314207HCID 90314207, compound

Product 1

HCID 90313722HCID 90313722, compound

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using 5-bromo-1H-pyrrolo[2,3-b]pyridine and 3′-fluoro-N-(2-hydroxyethyl)-4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-2-sulfonamide. MS (ESI): mass calcd. for C21H18FN3O3S, 411.11; m/z found, 412.0 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.44-8.41 (m, 1H), 8.24-8.21 (m, 1H), 8.14-8.05 (dd, J=8.0, 1.3, 1H), 7.71-7.64 (m, 1H), 7.63-7.55 (m, 2H), 7.46-7.44 (d, J=3.5, 1H), 7.44-7.41 (dd, J=7.6, 1.2, 1H), 7.36-7.34 (dd, J=3.8, 1.7, 1H), 7.34-7.31 (dd, J=7.3, 1.4, 1H), 6.59-6.55 (d, J=3.5, 1H), 3.52-3.47 (t, J=5.9, 2H), 2.92-2.87 (t, J=5.9, 2H).

Sources & evidence

ORD record: ord-18e274e655d5406abfe33dbc0a342fca
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079866B2

Reaction notes

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