Boron tribromide → HCID 67448217, compound

HRID 1853870Notes

Reaction equation

HRID 1853870 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[S:21][C:20]([CH2:22][NH:23]C(=O)OC(C)(C)C)=[CH:19][CH:18]=1.BrB(Br)Br>>[NH2:23][CH2:22][C:20]1[S:21][C:17]([C:4]2[C:5]3[C:6]4[CH:16]=[CH:15][S:14][C:7]=4[C:8](=[O:13])[NH:9][C:10]=3[CH:11]=[CH:12][C:3]=2[OH:2])=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 89682167HCID 89682167, compound

Product 1

HCID 67448217HCID 67448217, compoundYield 113.6%

Procedure

Following General Procedure F, tert-butyl [5-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)thiophen-2-yl]methylcarbamate (30 mg, 0.067 mmol) was reacted with tribromoborane (0.50 mL) to afford the desired product (25 mg, 91%) as a off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.67 (d, J=5.4 Hz, 1H), 7.43 (d, J=9.0 Hz, 1H), 7.16-7.14 (m, 2H), 6.86 (d, J=3.5 Hz, 1H), 6.35 (d, J=5.4 Hz, 1H), 4.12 (s, 2H); ESI MS m/z 329 [C16H12N2O2S2+H]+; HPLC 95.6% (AUC), tR=9.59 min.

Sources & evidence

ORD record
ord-d5b1a2ac1ad24be3994ce699a19e2995
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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