Potassium Carbonate → HCID 67503625, compound

HRID 1047026Notes

Reaction equation

HRID 1047026 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[NH:8][C:7]3[N:15]=[CH:16][CH:17]=[CH:18][C:6]=3[N:5]2[C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([C:26]2([NH:30]C(=O)OC(C)(C)C)[CH2:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.[CH3:38][O:39][C:40]1[CH:45]=[CH:44][C:43]([SH:46])=[CH:42][CH:41]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:38][O:39][C:40]1[CH:45]=[CH:44][C:43]([S:46][C:2]2[N:3]=[C:4]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[NH:8][C:7]4[N:15]=[CH:16][CH:17]=[CH:18][C:6]=4[N:5]3[C:19]=2[C:20]2[CH:21]=[CH:22][C:23]([C:26]3([NH2:30])[CH2:29][CH2:28][CH2:27]3)=[CH:24][CH:25]=2)=[CH:42][CH:41]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 127654-MethoxybenzenethiolHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 136331865tert-butyl {1-[4-(2-bromo-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate

Product 1

HCID 67503625HCID 67503625, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of tert-butyl {1-[4-(2-bromo-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (50 mg, 0.09 mmol), 4-methoxythiophenol (0.022 mL, 0.18 mmol), Pd2(dba)3 (8 mg, 0.01 mmol), xantphos (10 mg, 0.02 mmol), and K2CO3 (25 mg, 0.18 mmol) in DMF (0.9 mL) was heated at 160° C. for 1 hour. After cooling to room temperature, the mixture was purified by HPLC to give the titled compound as a white solid (9 mg, 15%). 1HNMR (CD3OD) 400 MHz δ: 8.33 (s, 2H), 8.11 (dd, J=4.6, 1.7 Hz, 1H), 7.90 (dd, J=7.7, 1.4 Hz, 1H), 7.50 (d, J=8.6 Hz, 2H), 7.40-7.33 (m, 3H), 7.19-7.11 (m, 4H), 7.02 (dd, J=8.0, 1.7 Hz, 1H), 6.81 (td, J=6.0, 3.4 Hz, 2H), 6.73 (dd, J=8.0, 4.6 Hz, 1H), 3.73 (s, 3H), 2.81-2.73 (m, 2H), 2.62-2.55 (m, 2H), 2.28-2.19 (m, 1H), 2.02-1.92 (m, 1H); LCMS: 518 [M+H].

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-10e837da5ca24d26950a43e38fddc757
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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