1,1'-Biphenyl-4-yl-boronic acid → 1-biphenyl-4-yl-2-chloro-1H-indole-3-carboxaldehyde

HRID 1678171Notes

Reaction equation

HRID 1678171 reaction equation
[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:13]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1>>[C:13]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:18]=[CH:17][C:16]([N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:10]([CH:11]=[O:12])=[C:2]2[Cl:1])=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 3147912-chloro-1H-indole-3-carbaldehyde

Product 1

HCID 860358961-biphenyl-4-yl-2-chloro-1H-indole-3-carboxaldehydeYield 52%

Procedure

2-Chloro-1H-indole-3-carboxaldehyde is reacted with 4-biphenylboronic acid as described in Step 1 of Example 29 to afford 1-biphenyl-4-yl-2-chloro-1H-indole-3-carboxaldehyde (52% yield) as a yellow solid. ESI/MS 332 (M+H), RT=4.14 min; NMR 10.15 (1H, s); 8.23 (1H, d, J=9 Hz); 7.99 (2H, d, J=9 Hz); 7.82 (2H, d, J=9 Hz); 7.69 (7H, m); 7.54 (1H, m).

Sources & evidence

ORD record
ord-ecff23c79b234dcdab067e83276de845
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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