2-Bromo-3-chloro-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one → 3-Chloro-2-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097416Notes

Reaction equation

HRID 2097416 reaction equation
Br[C:2]1[N:11]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:5]2[CH:6]=[N:7][NH:8][C:9](=[O:10])[C:4]=2[C:3]=1[Cl:20].BrC1N(COCC[Si](C)(C)C)C2C=NNC(=O)C=2C=1.[CH:40]1([CH2:43][O:44][C:45]2[CH:46]=[C:47](B(O)O)[CH:48]=[CH:49][C:50]=2[O:51][CH:52]([F:54])[F:53])[CH2:42][CH2:41]1.C1(OC2C=C(B3OC(C)(C)C(C)(C)O3)C=CC=2OC(F)F)CC1>>[Cl:20][C:3]1[C:4]2[C:9](=[O:10])[NH:8][N:7]=[CH:6][C:5]=2[N:11]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:2]=1[C:47]1[CH:48]=[CH:49][C:50]([O:51][CH:52]([F:54])[F:53])=[C:45]([O:44][CH2:43][CH:40]2[CH2:42][CH2:41]2)[CH:46]=1

Participants

5

Reactant 4

HCID 666025552-Bromo-3-chloro-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 666026402-Bromo-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneHCID 666028303-Cyclopropylmethoxy-4-difluoromethoxyphenylboronic acidHCID 666028342-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Product 1

HCID 666024603-Chloro-2-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 46%

Procedure

Reaction and post treatment were carried out in the same manner as in Example 1-(a) except for using 0.40 g (1.1 mmol) of 2-bromo-3-chloro-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in the following Reference example 16-(d) in place of 2-bromo-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo-[2,3-d]pyridazin-4-one, and using 0.55 g (2.1 mmol) of 3-cyclopropylmethoxy-4-difluoromethoxyphenylboronic acid obtained in the following Reference example 3-(b) in place of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, whereby 254 mg of the title compound was obtained as a white solid. (Yield: 46%)

Workup

  1. customReaction and post treatment

Sources & evidence

ORD record
ord-65300a002a5e41088d9bcca5cf6e9f7b
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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