Iodoethane → Methyl Acetate

HRID 1445907Notes

Reaction equation

[C:1]([O:5][C:6](=[O:28])[CH:7]([O:10][C:11]1[C:16]2[CH:17]=[C:18]([CH3:27])[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]=2[CH:14]=[CH:13][N:12]=1)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].[C:29]([O:33][C:34](=[O:54])[CH2:35]OC1C2C=C(C)N(CC3C=CC=CC=3)C=2C=CN=1)(C)(C)C.ICC>O1CCCC1>[C:1]([O:5][C:6](=[O:28])[CH:7]([O:10][C:11]1[C:16]2[CH:17]=[C:18]([CH3:27])[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]=2[CH:14]=[CH:13][N:12]=1)[CH2:8][CH3:9])([CH3:4])([CH3:2])[CH3:3].[CH3:29][O:33][C:34](=[O:54])[CH3:35]

Participants

Conditions

Temperature: -78 °C

Procedure

2-(1-Benzyl-2-methyl-1H-pyrrolo[3,2-c]pyridin-4-yloxy)-butyric acid tert-butyl ester, 15: (1-Benzyl-2-methyl-1H-pyrrolo[3,2-c]pyridin-4-yloxy)-acetic acid tert-butyl ester, 14 (200 mg, 0.568 mmol) was dissolved in a dry tetrahydrofuran (10 mL) and then cooled to −78° C. To the mixture the tetrahydrofuran solution (1.0 M) of LiN(Si(CH3)3)2 (1.70 mL) was added dropwise at −78° C. The reaction mixture was stirred from −78° C. to −5° C. for 1 h and then the tetrahydrofuran solution (5 mL) of iodoethane (0.15 mL, 1.84 mmol) was added dropwise at −50° C. The mixture was stirred for 4 h from −50° C. to room temperature. The mixture was concentrated and the residue was purified by silica gel chromatography (hexane to hexane:ethyl acetate, 4:1) to afford 2-(1-benzyl-2-methyl-1H-pyrrolo[3,2-c]pyridin-4-yloxy)-butyric acid tert-butyl ester, 15 Yield: 50 mg, (23%)

Workup

stirringThe mixture was stirred for 4 h from −50° C. to room temperature
concentrationThe mixture was concentrated
customthe residue was purified by silica gel chromatography (hexane to hexane:ethyl acetate, 4:1)

Sources & evidence

ORD record: ord-eea9585901bd4815a882ffac45e8706b
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666898B2

Reaction notes

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