Ethanol → HCID 22508891, compound

HRID 2111774Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:7]([CH3:27])=[C:8]2[N:13]([CH:14]=1)[N:12]=[CH:11][N:10]=[C:9]2[O:15][C:16]1[C:17]([F:26])=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH3:25])=[CH:19]2)=O)C.CC(C[AlH]CC(C)C)C.C(O)C>C(Cl)Cl>[F:26][C:17]1[C:16]([O:15][C:9]2[C:8]3=[C:7]([CH3:27])[C:6]([CH2:4][OH:3])=[CH:14][N:13]3[N:12]=[CH:11][N:10]=2)=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[C:20]([CH3:25])[NH:21]2

Participants

Conditions

Temperature: -15 °C

Procedure

To a solution of 4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-5-methyl-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid ethyl ester (68 mg 0.19 mmol) in anhydrous methylene chloride (2.0 mL) at −78° C. under argon was added DIBAL (0.48 mmol, 0.48 mL, 1.0M, 2.5 eq.) dropwise. After 5 minutes, the mixture was warmed to −15° C. and allowed to stir for an additional 15 minutes. A drop of ethanol was added to quench the reaction followed by 1N sodium hydroxide (0.2 mL) and 1.0 mL of ethyl acetate and 1.0 mL of THF. After 30 minutes, the mixture was filtered to remove the resulting solid. The filtrate was dried, concentrated in vacuo, and chromatographed using silica gel eluting with 40-75% ethyl acetate in hexanes (gradient). Concentration of the desired fractions afforded the title compound (39 mg, 63%) as a clear oil. LC/MS; (M+H)+=327.3

Workup

customto quench the reaction
waitAfter 30 minutes
filtrationthe mixture was filtered
customto remove the resulting solid
customThe filtrate was dried
concentrationconcentrated in vacuo
customchromatographed

Sources & evidence

ORD record: ord-b476f4d6485640ddaca7e265475112bf
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521450B2

Reaction notes

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