Phenylboronic Acid → Ethyl 1-benzyloxymethyl-5-(3-cyclopropoxy-4-difluoromethoxyphenyl)-2-formyl-4-(6-methoxy-3-pyridylmethyl)-1H-pyrrol-3-carboxylate

HRID 2097528Notes

Reaction equation

HRID 2097528 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:14](Br)=[C:13]([CH2:16][C:17]2[CH:18]=[N:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[C:12]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:11]1[CH:30]=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1N(COCC[Si](C)(C)C)C2C=NNC(=O)C=2C=1I.[CH:52]1([O:55][C:56]2[CH:57]=[C:58](B3OC(C)(C)C(C)(C)O3)[CH:59]=[CH:60][C:61]=2[O:62][CH:63]([F:65])[F:64])[CH2:54][CH2:53]1.C1(B(O)O)C=CC=CC=1>>[CH2:1]([O:8][CH2:9][N:10]1[C:14]([C:58]2[CH:59]=[CH:60][C:61]([O:62][CH:63]([F:65])[F:64])=[C:56]([O:55][CH:52]3[CH2:53][CH2:54]3)[CH:57]=2)=[C:13]([CH2:16][C:17]2[CH:18]=[N:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[C:12]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:11]1[CH:30]=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 66827Phenylboronic AcidHCID 666028262-Chloro-3-iodo-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 666028342-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolaneHCID 77230465Ethyl 5-bromo-2-formyl-4-[(6-methoxy-3-pyridinyl)methyl]-1-(phenylmethoxymethyl)pyrrole-3-carboxylate

Product 1

HCID 86627051Ethyl 1-benzyloxymethyl-5-(3-cyclopropoxy-4-difluoromethoxyphenyl)-2-formyl-4-(6-methoxy-3-pyridylmethyl)-1H-pyrrol-3-carboxylateYield 96%

Procedure

Reaction and post treatment were carried out in the same manner as in Reference example 31 except for using 322 mg (0.66 mmol) of ethyl 1-benzyloxymethyl-5-bromo-2-formyl-4-(6-methoxy-3-pyridylmethyl)-1H-pyrrol-3-carboxylate obtained in Reference example 43-(b) in place of 2-chloro-3-iodo-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo-[2,3-d]pyridazin-4-one, and using 323 mg (0.96 mmol) of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane obtained in Reference example 1-(a) in place of phenylboronic acid, respectively, whereby 383 mg of the title compound was obtained as a slightly yellowish oil. (Yield: 96%)

Workup

  1. customReaction and post treatment

Sources & evidence

ORD record
ord-50a302d3637e43e5968f959ae03ad8a6
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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