(4-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol → 4-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

HRID 1912552Notes

Reaction equation

HRID 1912552 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:16]([CH2:17][OH:18])=[C:15]([CH3:19])[N:14]=[C:13]4[N:20]([CH2:23][C:24]5[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=5)[CH:21]=[CH:22][C:12]=34)=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[O:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:16]([CH:17]=[O:18])=[C:15]([CH3:19])[N:14]=[C:13]4[N:20]([CH2:23][C:24]5[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=5)[CH:21]=[CH:22][C:12]=34)=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 71209165(4-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 866757424-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of (4-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol (967 mg, 2.300 mmol) in dichloromethane (DCM) (24 mL) was treated with PCC (644 mg, 2.99 mmol) and the mixture was stirred at ambient temperature for 90 minutes. The mixture was diluted with dichloromethane, filtered over Celite™ and the filtrate was concentrated. The residue was purified on silica gel (0-70% ethyl acetate/hexanes) to afford the desired product as a pale yellow foam: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.11 (s, 1 H), 7.22 (dd, J=2.1, 8.4 Hz, 1 H), 7.16-7.04 (m, 4 H), 7.04-6.97 (m, 1 H), 6.93 (d, J=8.4 Hz, 1 H), 6.44 (d, J=3.5 Hz, 1 H), 5.47 (s, 2 H), 4.37-4.20 (m, 2 H), 2.95 (s, 3 H), 2.86 (t, J=6.4 Hz, 2 H), 2.20-1.96 (m, 2 H); LC/MS (m/z) ES+=419 (M+1).

Workup

  1. filtrationfiltered over Celite™
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified on silica gel (0-70% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-604e89c35b4f49748ebda284243de9c0
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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