HCID 2757034, compound → HCID 10156605, compound

HRID 1061793Notes

Reaction equation

HRID 1061793 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.COC1C=C(C2C=CC=C(B3OCC(C)(C)CO3)C=2)C=CC=1.Cl[C:39]1[CH:48]=[CH:47][N:46]=[C:45]2[C:40]=1[CH:41]=[CH:42][C:43]([C:49]([F:52])([F:51])[F:50])=[N:44]2>>[CH3:15][O:14][C:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:39]3[CH:48]=[CH:47][N:46]=[C:45]4[C:40]=3[CH:41]=[CH:42][C:43]([C:49]([F:52])([F:50])[F:51])=[N:44]4)[CH:3]=2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 2757034HCID 2757034, compoundHCID 222852765-chloro-2-(trifluoromethyl)-1,8-NaphthyridineHCID 22285315HCID 22285315, compound

Product 1

HCID 10156605HCID 10156605, compoundYield 13%

Procedure

3-Bromo-3′-methoxybiphenyl (prepared as described in patent WO 0130764) was converted to 2-(3′-methoxybiphenyl-3-yl)-5,5-dimethyl[1,3,2]-dioxaborinane using the procedure described in Example 7 part f). The crude product of this transformation (83 mg, 0.28 mmol) was coupled to 5-chloro-2-trifluoromethyl[1,8]-naphthyridine (50 mg, 0.22 mmol) as described in Example 7 part g), affording 5-(3′-methoxybiphenyl-3-yl)-2-trifluoromethyl[1,8]naphthyridine (11 mg, 13%). δH (360 MHz, CDCl3) 3.87 (3H, s), 6.95 (1H, m), 7.14-7.25 (2H, m), 7.40 (1H, t, J 7.9), 7.47 (1H, d, J 7.7), 7.56-7.69 (3H, m), 7.77-7.83 (2H, m), 8.59 (1H, d, J 8.8), 9.29 (1H, d, J 4.2). m/z (ES+) 381 [MH]

Sources & evidence

ORD record
ord-c1e5e71362a14ab7b660e792626e3e75
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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