Boron tribromide → HCID 67448171, compound

HRID 1853869Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]3[C:10]4[CH:23]=[CH:22][S:21][C:11]=4[C:12](=[O:20])[NH:13][C:14]=3[CH:15]=[CH:16][C:17]=2[O:18]C)[CH:5]=[CH:4][C:3]=1[S:24]([NH:27][CH2:28][CH2:29]O)(=[O:26])=[O:25].[Br:31]B(Br)Br>>[Br:31][CH2:29][CH2:28][NH:27][S:24]([C:3]1[CH:4]=[CH:5][C:6]([C:8]2[C:9]3[C:10]4[CH:23]=[CH:22][S:21][C:11]=4[C:12](=[O:20])[NH:13][C:14]=3[CH:15]=[CH:16][C:17]=2[OH:18])=[CH:7][C:2]=1[F:1])(=[O:26])=[O:25]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 67447616HCID 67447616, compound

Product 1

HCID 67448171HCID 67448171, compoundYield 81%

Procedure

Following General Procedure F, 2-fluoro-N-(2-hydroxyethyl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (52 mg, 0.12 mmol) was reacted with tribromoborane (0.80 mL, 0.23 mmol) to afford the desired product (47 mg, 81%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 11.86 (s, 1H), 9.52 (s, 1H), 8.45 (t, J=5.7 Hz, 1H), 7.92 (t, J=7.8 Hz, 1H), 7.80 (d, J=5.5 Hz, 1H), 7.46 (d, J=10.9 Hz, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.30 (dd, J=8.0, 1.4 Hz, 1H), 7.19 (d, J=9.0 Hz, 1H), 6.00 (d, J=5.4 Hz, 1H), 3.53 (t, J=6.3 Hz, 2H), 3.42 (q, J=6.0 Hz, 2H); ESI MS m/z 499 [C19H14BrFN2O4S2+H]+; HPLC 98.3% (AUC), tR=15.61 min.

Sources & evidence

ORD record: ord-4122229060a54c629042cf8337131f29
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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