2-Bromo-3-chloro-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one → 3-Chloro-2-(8-difluoromethoxy-2,2-dimethyl-2H-chromen-5-yl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097432Notes

Reaction equation

HRID 2097432 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.[F:40][CH:41]([F:64])[O:42][C:43]1[CH:44]=[CH:45][C:46](B2OC(C)(C)C(C)(C)O2)=[C:47]2[C:52]=1[O:51][C:50]([CH3:54])([CH3:53])[CH:49]=[CH:48]2.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:46]1[CH:45]=[CH:44][C:43]([O:42][CH:41]([F:40])[F:64])=[C:52]2[C:47]=1[CH:48]=[CH:49][C:50]([CH3:54])([CH3:53])[O:51]2

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 666026762-(8-difluoromethoxy-2,2-dimethyl-2H-chromen-5-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolaneHCID 666028342-(3-Cyclopropoxy-4-difluoromethoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Product 1

HCID 666028733-Chloro-2-(8-difluoromethoxy-2,2-dimethyl-2H-chromen-5-yl)-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 70%

Procedure

Reaction and post treatment were carried out in the same manner as in Example 1-(a) except for using 189 mg (0.500 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 352 mg (1.00 mmol) of 2-(8-difluoromethoxy-2,2-dimethyl-2H-chromen-5-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane obtained in the following Reference example 1-(i) in place of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, whereby 183 mg of the title compound was obtained as a pale yellowish foam. (Yield: 70%)

Workup

  1. customReaction and post treatment

Sources & evidence

ORD record
ord-04516fb6dd0f4f9bb249203ffb431874
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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