Phenylboronic Acid → 6-Acetyl-5,6-dihydro-3-phenylpyrido[4,3-c][1]benzazocine

HRID 2224332Notes

Reaction equation

HRID 2224332 reaction equation
[C:1]([N:4]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[CH:8][C:7]2[CH:16]=[N:17][C:18](Cl)=[CH:19][C:6]=2[CH2:5]1)(=[O:3])[CH3:2].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N1C2C=CC=CC=2C=CC2N=C(C3C=NC(OC)=CC=3)C(F)=CC=2C1)(=O)C>>[C:1]([N:4]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[CH:8][C:7]2[CH:16]=[N:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:19][C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 66827Phenylboronic AcidHCID 692911976-Acetyl-3-fluoro-5,6-dihydro-2-(6-methoxy-3-pyridinyl)-pyrido[3,2-c][1]benzazocineHCID 723667836-Acetyl-3-chloro-5,6-dihydropyrido[4,3-c][1]benzazocine

Product 1

HCID 692909306-Acetyl-5,6-dihydro-3-phenylpyrido[4,3-c][1]benzazocineYield 70%

Procedure

The title compound (12.0 mg, 70%) was prepared from 25E (15.0 mg, 0.053 mmol) and phenylboronic acid (9.6 mg, 0.079 mmol) by a route analogous to that used for the preparation of 2B. HPLC Rt=2.356 min; LCMS Found: (M+H)+=327.

Sources & evidence

ORD record
ord-43c9b792544d404f924b1a04dfe1d473
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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