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

HRID 1912546Notes

Reaction equation

HRID 1912546 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:16]([C:17](OC)=[O:18])=[C:15]([CH3:21])[N:14]=[C:13]4[NH:22][CH:23]=[CH:24][C:12]=34)=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>O1CCCC1.CCOC(C)=O>[O:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:16]([CH2:17][OH:18])=[C:15]([CH3:21])[N:14]=[C:13]4[NH:22][CH:23]=[CH:24][C:12]=34)=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 71209166methyl 4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

An ice cooled mixture of methyl 4-(chroman-6-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (519 mg, 90%, 1.449 mmol) in tetrahydrofuran (THF) (10 mL) was treated with LAH (4.35 mL, 4.35 mmol) (2:00 pm) and the mixture was stirred overnight at ambient temperature. The reaction mixture was cooled to 0° C. Added water (160 uL) then stirred several minutes. Then, 15% NaOH (160 uL) was added and stirred several minutes. Finally, added water (480 uL) and stirred 5 minutes. The mixture was diluted with EtOAc, filtered over Celite™ and the filtrate was concentrated to afford the crude (4-(chroman-6-yl)-6-methyl-1 H-pyrrolo[2,3-b]pyridin-5-yl)methanol which was used without further purification: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.51 (br. s., 1 H), 7.26-7.15 (m, 3 H), 6.92 (d, J=8.4 Hz, 1 H), 6.29 (d, J=2.3 Hz, 1 H), 4.75 (s, 2 H), 4.31-4.26 (m, 2 H), 2.91-2.83 (m, 5 H), 2.13-2.07 (m, 2 H); LC/MS (m/z) ES+=295.26 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C
  2. stirringstirred several minutes
  3. stirringstirred 5 minutes
  4. filtrationfiltered over Celite™
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0ba48b8a0ab54cfe8d20563a1015debf
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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