Dibenzothiophene-4-boronic acid → 1-benzyl-5-(dibenzo[b,d]thien-4-ylamino)-3-phenyl-1H-indole-2-carboxylic acid

HRID 2055743Notes

Reaction equation

HRID 2055743 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([C:18]([O:20]CC)=[O:19])=[C:5]2[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH:29]1[C:37]2[C:36]3[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=3[S:34][C:33]=2[C:32](B(O)O)=[CH:31][CH:30]=1>>[CH2:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][C:32]3[C:33]4[S:34][C:35]5[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=5[C:37]=4[CH:29]=[CH:30][CH:31]=3)=[CH:10][CH:9]=2)[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:6]1[C:18]([OH:20])=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 2734329Dibenzothiophene-4-boronic acidHCID 69229300ethyl 5-amino-1-benzyl-3-phenyl-1H-indole-2-carboxylate

Product 1

HCID 114211211-benzyl-5-(dibenzo[b,d]thien-4-ylamino)-3-phenyl-1H-indole-2-carboxylic acid

Procedure

The title compound was prepared from ethyl 5-amino-1-benzyl-3-phenyl-1H-indole-2-carboxylate and 4-dibenzothiopheneboronic acid according to the procedure of Example 1 Step 3 as a black solid: 1H NMR (DMSO-d6) δ 5.82 (s, 2 H), 7.00-8.20 (m, 27 H); MS (ESI) m/z 525 (MH+); HRMS calcd. for C34H25N2O2S: 525.1637; found (ESI+): 525.1622; Anal. calcd. for C34H24N2O2S.0.3ACN: C, 74.88; H, 4.89; N, 5.81. Found: C, 75.14; H, 4.53; N, 5.82.

Sources & evidence

ORD record
ord-a41f7451aab74369a83b8fd08848d20a
Source dataset
uspto-grants-2008_02
Patent number
US07332521B2

Reaction notes

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