2-(6-Chloro-3-methoxy-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester → 2-{6-[3-Formyl-5-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-3-methoxy-pyridazin-4-yl}-indole-1-carboxylic acid tert-butyl ester

HRID 2234139Notes

Reaction equation

HRID 2234139 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:20][CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[C:5]([CH:8]=[C:9](B2OC(C)(C)C(C)(C)O2)[CH:10]=1)[CH:6]=[O:7].[C:29]([O:33][C:34]([N:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[C:37]1[C:45]1[CH:50]=[C:49](Cl)[N:48]=[N:47][C:46]=1[O:52][CH3:53])=[O:35])([CH3:32])([CH3:31])[CH3:30]>>[C:29]([O:33][C:34]([N:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[C:37]1[C:45]1[CH:50]=[C:49]([C:9]2[CH:10]=[C:3]([O:2][CH3:1])[C:4]([O:20][CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:26])([CH3:27])[CH3:28])=[C:5]([CH:6]=[O:7])[CH:8]=2)[N:48]=[N:47][C:46]=1[O:52][CH3:53])=[O:35])([CH3:32])([CH3:31])[CH3:30]

Participants

3

Reactant 2

HCID 866120482-(6-Chloro-3-methoxy-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl esterHCID 866120613-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-(2-trimethylsilanyl-ethoxymethoxy)-benzaldehyde

Product 1

HCID 866120602-{6-[3-Formyl-5-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-3-methoxy-pyridazin-4-yl}-indole-1-carboxylic acid tert-butyl ester

Procedure

400 mg of 3-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-(2-trimethylsilanyl-ethoxymethoxy)-benzaldehyde and 353 mg of 2-(6-Chloro-3-methoxy-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester is reacted analogously to the procedure described in Example 126(a). Yield 377 mg. LC-MS (ES+) 606 (M+H)+.

Sources & evidence

ORD record
ord-230e016a2eb9462d893e94df0d44072d
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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