Phenylboronic Acid → 6-Acetyl-3-fluoro-5,6-dihydro-2-phenylpyrido[3,2-c][1]benzazocine

HRID 2224304Notes

Reaction equation

HRID 2224304 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[N:16]=[C:17](Cl)[C:18]([F:20])=[CH:19][C:6]=2[CH2:5]1)(=[O:3])[CH3:2].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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[N:16]=[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18]([F:20])=[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 743934126-Acetyl-2-chloro-3-fluoro-5,6-dihydro-pyrido[3,2-c][1]benzazocine

Product 1

HCID 692915246-Acetyl-3-fluoro-5,6-dihydro-2-phenylpyrido[3,2-c][1]benzazocineYield 88.5%

Procedure

The title compound (20.1 mg, 88.5%) was prepared from 1D (20.0 mg, 0.066 mmol) and phenylboronic acid (12.1 mg, 0.099 mmol) by a route analogous to that used for the preparation of 2B. HPLC Rt=3.326 min; LCMS Found: (M+H)+=345.

Sources & evidence

ORD record
ord-0514339962b84035bce4b9a411795892
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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