Triacetoxyperiodinane → 1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-6-(morpholine-4-carbonyl)-1H-indole-3-carbaldehyde

HRID 630456Notes

Reaction equation

HRID 630456 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[CH:31]=[N:32][C:33]([N:36]2[C:44]3[C:39](=[CH:40][CH:41]=[C:42]([C:45]([N:47]4[CH2:52][CH2:51][O:50][CH2:49][CH2:48]4)=[O:46])[CH:43]=3)[C:38]([CH2:53][OH:54])=[CH:37]2)=[N:34][CH:35]=1>ClCCl>[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:30]1[CH:35]=[N:34][C:33]([N:36]2[C:44]3[C:39](=[CH:40][CH:41]=[C:42]([C:45]([N:47]4[CH2:52][CH2:51][O:50][CH2:49][CH2:48]4)=[O:46])[CH:43]=3)[C:38]([CH:53]=[O:54])=[CH:37]2)=[N:32][CH:31]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 118666239(1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(hydroxymethyl)-1H-indol-6-yl)(morpholino)methanone

Product 1

HCID 1186660411-(5-(2-Fluorophenyl)pyrimidin-2-yl)-6-(morpholine-4-carbonyl)-1H-indole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess Martin periodinane (235 mg, 0.556 mmol, 1.5 eq) was added to the product of 27d) (160 mg, 0.370 mmol, 1.0 eq) in dichloromethane (10 mL) at 0° C. The mixture was stirred for 2 h at room temperature, and then filtered through a pad of celite. The filter was rinsed with dichloromethane and the filtrate was dried over sodium sulfate, and evaporated. White solid. Yield: 140 mg. Mass spectroscopy: m/z: [M+H]+=430.9

Workup

  1. filtrationfiltered through a pad of celite
  2. washThe filter was rinsed with dichloromethane
  3. dry with materialthe filtrate was dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-5f8e79dadb154c1dbdc1a9f8ace3ce40
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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