2-Thiopheneboronic acid → HCID 9921542, compound

HRID 33338Notes

Reaction equation

HRID 33338 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:19](=[O:20])[NH:18][CH2:17][CH2:16][C:15]=2[C:14]=34)C=C[CH:4]=[CH:3][CH:2]=1.[S:21]1C=CC=C1B(O)O>>[S:21]1[CH:4]=[CH:3][CH:2]=[C:1]1[C:7]1[NH:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:19](=[O:20])[NH:18][CH2:17][CH2:16][C:15]=1[C:14]=23

Participants

3

Reactant 2

HCID 27339602-Thiopheneboronic acidHCID 102208822-Phenyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-9-one

Product 1

HCID 9921542HCID 9921542, compound

Procedure

In a manner similar to that described for Compound 12, the tricyclic bromide (300 mg, 1.13 mmol) and thiophene-2-boronic acid (159 mg, 1.24 mmol) were coupled to yield 2-thiophen-2-yl-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one, 171 mg (56%) as a beige solid: m.p. 220.5-222.5° C.; 1H NMR (300 MHz d6-DMSO) δ 3.08 (m, 2H), 3.48 (m, 2H), 7.23 (m, 2H), 7.52 (m, 2H), 7.69 (m, 2H), 8.05 (br t, 1H), 11.60 (br s, 1H). MS (electrospray, MH+) 269. Anal. (C15H12N2)S 0.8 H2O) C, H, N.

Sources & evidence

ORD record
ord-970d62668c2a4107bfef79a0e8a1d2af
Source dataset
uspto-grants-2008_09
Patent number
US07429578B2

Reaction notes

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