Boron tribromide → HCID 53472625, compound

HRID 1853884Notes

Reaction equation

C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]3[C:17]4[CH:30]=[CH:29][S:28][C:18]=4[C:19](=[O:27])[NH:20][C:21]=3[CH:22]=[CH:23][C:24]=2[O:25]C)=[CH:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C.BrB(Br)Br>>[OH:25][C:24]1[CH:23]=[CH:22][C:21]2[NH:20][C:19](=[O:27])[C:18]3[S:28][CH:29]=[CH:30][C:17]=3[C:16]=2[C:15]=1[C:12]1[CH:11]=[CH:10][C:9]([S:6]([NH2:5])(=[O:8])=[O:7])=[CH:14][CH:13]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 67448894HCID 67448894, compound

Product 1

HCID 53472625HCID 53472625, compoundYield 94%

Procedure

Following General Procedure F, N-tert-butyl-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (4.3 g, 9.9 mmol) was reacted with tribromoborane (1.0 M in methylene chloride, 48 mL, 48 mmol) to afford the desired product (3.4 g, 94%) as a light red solid: 1H NMR (300 MHz, DMSO-d6) δ 11.83 (s, 1H), 9.12 (s, 1H), 7.96-7.95 (m, 2H), 7.76 (d, J=5.4 Hz, 1H), 7.48-7.47 (m, 4H), 7.41 (d, J=8.9 Hz, 1H), 7.18 (d, J=8.9 Hz, 1H), 5.91 (d, J=5.4 Hz, 1H); ESI MS m/z 373 [C17H12N2O4S2+H]+; HPLC 98.1% (AUC), tR=10.29 min.

Sources & evidence

ORD record: ord-666f703c6c3c4e40b497cc6e0bbad465
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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