Trifluoroacetic acid → HCID 18373253, compound

HRID 2301665Notes

Reaction equation

[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([Cl:23])[CH:21]=2)[CH:16]=[CH:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24]([C:26]1[CH:37]=[C:36]([CH3:38])[C:29]([O:30][CH2:31][C:32]([O:34]C)=[O:33])=[C:28]([CH3:39])[CH:27]=1)=O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([Cl:23])[CH:21]=2)[C:16]([CH2:24][C:26]2[CH:37]=[C:36]([CH3:38])[C:29]([O:30][CH2:31][C:32]([OH:34])=[O:33])=[C:28]([CH3:39])[CH:27]=2)=[CH:15]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To 1-benzhydryl-6-chloro-1H-indole (1.0 eq) and methyl 2-(4-formyl-2,6-dimethylphenoxy)acetate (0.6 eq) in CH2Cl2 (0.1M) at 0° C. was added neat triethysilane (3 eq) followed by triflouroacetic acid (3 eq). After 10 minutes at 0° C. the reaction was warmed to room temperature and stirred until the initially formed spot by TLC yields a new spot. The reaction was then quenched by the addition of saturated sodium bicarbonate, diluted with CH2Cl2 and washed with saturated sodium bicarbonate, water and brine, dried over magnesium sulfate and purified by column chromatography to yield 89% of the desired product.

Workup

customyields a new spot
customThe reaction was then quenched by the addition of saturated sodium bicarbonate
additiondiluted with CH2Cl2
washwashed with saturated sodium bicarbonate, water and brine
dry with materialdried over magnesium sulfate
custompurified by column chromatography

Sources & evidence

ORD record: ord-c6d28c2096ae4d89a8683f7288004d1a
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500853B1

Reaction notes

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