Phenylboronic Acid → 3-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine

HRID 1046995Notes

Reaction equation

HRID 1046995 reaction equation
[N:1]1[CH:2]=[C:3]([C:19]2[CH:24]=[CH:23][C:22](C3(NC(=O)OC(C)(C)C)CCC3)=[CH:21][CH:20]=2)[N:4]2[C:10]=1[C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[NH:7][C:6]1[N:15]=[CH:16][CH:17]=[CH:18][C:5]2=1.C1(B(O)O)C=CC=CC=1>>[C:19]1([C:3]2[N:4]3[C:5]4[CH:18]=[CH:17][CH:16]=[N:15][C:6]=4[NH:7][C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=4[C:10]3=[N:1][CH:2]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 69087639tert-butyl {1-[4-(9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate

Product 1

HCID 675034233-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine

Procedure

The title compound was synthesized according to the procedure described in the synthesis of tert-butyl {1-[4-(9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (above) using phenylboronic acid instead of tert-butyl {1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclobutyl}carbamate. 1HNMR (DMSO-d6) 400 MHz δ: 8.58 (br s, 1H), 8.14 (dd, J=4.6, 1.7 Hz, 1H), 7.92-7.86 (m, 1H), 7.45 (s, 1H), 7.40-7.26 (m, 5H), 7.18-7.13 (m, 2H), 7.10-7.05 (m, 1H), 7.00-6.95 (m, 1H), 6.85 (dd, J=8.0, 4.6 Hz, 1H); LC/MS: 311 [M+H].

Sources & evidence

ORD record
ord-0fcb262844034d1faac5dd8a2980b2e1
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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