Boron tribromide → HCID 136164280, compound

HRID 1853885Notes

Reaction equation

HRID 1853885 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]3[C:11]4[C:12]5[CH:25]=[CH:24][S:23][C:13]=5[C:14](=[O:22])[NH:15][C:16]=4[CH:17]=[CH:18][C:19]=3[O:20]C)[CH:8]=2)[CH:3]=[N:2]1.BrB(Br)Br>>[OH:20][C:19]1[CH:18]=[CH:17][C:16]2[NH:15][C:14](=[O:22])[C:13]3[S:23][CH:24]=[CH:25][C:12]=3[C:11]=2[C:10]=1[C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[N:2][NH:1]2)=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 67448575HCID 67448575, compound

Product 1

HCID 136164280HCID 136164280, compoundYield 11%

Procedure

Following General Procedure F, 9-(1H-indazol-6-yl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one (35 mg, 0.10 mmol) was reacted with tribromoborane (1.5 mL, 0.15 mmol) to afford the desired product (3.6 mg, 11%) as a light brown solid: 1H NMR (500 MHz, CD3OD) δ 8.17 (s, 1H), 7.75-7.73 (m, 2H), 7.48 (d, J=5.5 Hz, 1H), 7.42 (d, J=8.9 Hz, 1H), 7.34 (d, J=9.2 Hz, 1H), 7.19 (d, J=8.9 Hz, 1H), 5.91 (d, J=5.5 Hz, 1H); ESI MS m/z 334 [C18H11N3O2S+H]+; HPLC 96.3% (AUC), tR=9.20 min.

Sources & evidence

ORD record
ord-100118a643b0405a81b7f9c1a713939b
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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