Triphenylphosphine → 8-{2-[(6-Chloropyridin-3-yl)oxy]ethyl}-3-(3-methoxy-4-nitrophenyl)-5,10-dihydro-11h-dibenzo[b,e][1,4]diazepin-11-one

HRID 272723Notes

Reaction equation

HRID 272723 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:13][C:12]3[CH:14]=[C:15]([C:18]4[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([O:27][CH3:28])[CH:19]=4)[CH:16]=[CH:17][C:11]=3[C:10](=[O:29])[NH:9][C:8]=2[CH:30]=1.[Cl:31][C:32]1[N:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1.CO.CS(C)=O>[Cl:31][C:32]1[N:37]=[CH:36][C:35]([O:1][CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]3[NH:13][C:12]4[CH:14]=[C:15]([C:18]5[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([O:27][CH3:28])[CH:19]=5)[CH:16]=[CH:17][C:11]=4[C:10](=[O:29])[NH:9][C:8]=3[CH:30]=2)=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 8198212-Chloro-5-hydroxypyridineHCID 69219945HCID 69219945, compound

Product 1

HCID 877378968-{2-[(6-Chloropyridin-3-yl)oxy]ethyl}-3-(3-methoxy-4-nitrophenyl)-5,10-dihydro-11h-dibenzo[b,e][1,4]diazepin-11-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

A mixture of Example 239 (41 mg, 0.1 mmol), 6-chloro-pyridin-3-ol (19 mg, 0.15 mmol), PPh3 (39 mg, 0.15 mmol), and di-tert-butyl azodicarboxylate (35 mg, 0.15 mmol) in THF (2 ml) was stirred at room temperature for 16 hours. The reaction mixture was diluted with MeOH/DMSO (1:1), and purified by preparative HPLC to provide the desired product. MS (ESI) m/e 517 (M+H)+; 1H NMR (499 MHz, DMSO-d6) δ 9.86 (s, 1H), 8.11 (d, J=3.12 Hz, 1H), 8.01 (d, J=8.42 Hz, 1H), 7.96 (s, 1H), 7.80 (d, J=8.11 Hz, 1H), 7.52 (s, 1H), 7.47 (m, 1H), 7.40 (d, J=8.73 Hz, 1H), 7.34 (m, 2H), 7.30 (dd, J=8.11, 1.56 Hz, 2H), 6.95 (m, 2H), 4.21 (t, J=6.55 Hz, 2H), 4.03 (s, 3H), 2.92 (t, J=6.55 Hz, 2H).

Workup

  1. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-45ab27c76330444eb531d0e106c9824c
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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