Bromobenzene → HCID 56946585, compound

HRID 2373432Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:11][C:10](=[O:12])[NH:9][C:8]3[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:7]=3[C:6]=2[N:18]=1.Br[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].O>[Cl:17][C:14]1[CH:15]=[CH:16][C:7]2[C:6]3[N:18]=[C:2]([NH:1][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:3]=[CH:4][C:5]=3[CH2:11][C:10](=[O:12])[NH:9][C:8]=2[CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-amino-9-chloro-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one (I-23) (148 mg, 0.568 mmol), 1-bromobenzene (0.072 mL, 0.681 mmol), Cs2CO3 (333 mg, 1.02 mmol), and BINAP (53 mg, 0.085 mmol) in 4 mL toluene was added Pd(OAc)2 (12.8 mg, 0.057 mmol), and the reaction was stirred at 100° C. for 12 h. The reaction mixture was then treated with H2O and extracted with CH2Cl2 (2×30 mL). The organic fractions were combined, filtered, dried over MgSO4 and concentrated in vacuo to give an orange oil which was purified by C-18 RP LC-MS chromatography to afford I-61 (0.9%): HRMS Calcd. for C18H13ClN4O: 337.0856, Found 337.0853.

Workup

extractionextracted with CH2Cl2 (2×30 mL)
filtrationfiltered
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto give an orange oil which
customwas purified by C-18 RP LC-MS chromatography
customto afford I-61 (0.9%)

Sources & evidence

ORD record: ord-e0b9a1bfaea94e3e97c0fc840e5a37fb
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459448B2

Reaction notes

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