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

HRID 1912547Notes

Reaction equation

HRID 1912547 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[NH:20][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[NH:20][CH:21]=[CH:22][C:12]=34)=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 71209302(4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 866757414-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehydeYield 37.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol in dichloromethane (DCM) (10 mL) was treated with PCC (469 mg, 2.174 mmol) and stirred at ambient temperature for 90 minutes. The reaction was judged complete by LCMS. The mixture was filtered over Celite and the filtrate was concentrated. Half of the residue was purified on a short column of silica gel (7.5 grams, 0-100% hex/EtOAc) to afford the desired product (159 mg, 0.544 mmol, 37.5%) as a yellow solid The rest, 212 mg of crude aldehyde, was used without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.12 (s, 1 H), 7.38-7.31 (m, 1 H), 7.25 (d, J=8.6 Hz, 1 H), 7.16 (s, 1 H), 6.96 (d, J=8.0 Hz, 1 H), 6.49 (s, 1 H), 4.33-4.27 (m, 2 H), 2.99 (br. s., 3 H), 2.88 (t, 2 H), 2.10 (quin, J=5.7 Hz, 2 H); LC/MS (m/z) ES+=293.24 (M+1).

Workup

  1. filtrationThe mixture was filtered over Celite
  2. concentrationthe filtrate was concentrated
  3. customHalf of the residue was purified on a short column of silica gel (7.5 grams, 0-100% hex/EtOAc)

Sources & evidence

ORD record
ord-766b9cb4f8b04497aa122d424ff81c4b
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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