Tetrahydrofuran → methyl 3-((1-(tert-butoxycarbonyl)piperidin-4-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

HRID 1627076Notes

Reaction equation

HRID 1627076 reaction equation
[CH:1]([C:3]1[C:11]2[C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=[N:7][C:6]=2[NH:5][CH:4]=1)=O.[NH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1.C1COCC1.[BH4-].[Na+]>CO>[C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][CH:17]([NH:16][CH2:1][C:3]2[C:11]3[C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=[N:7][C:6]=3[NH:5][CH:4]=2)[CH2:18][CH2:19]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 12682914-Amino-1-Boc-piperidineHCID 4311764Sodium borohydrideHCID 53412886methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

Product 1

HCID 67223926methyl 3-((1-(tert-butoxycarbonyl)piperidin-4-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylateYield 19.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylate (160 mg, 0.784 mmol) and tert-butyl 4-aminopiperidine-1-carboxylate (188 mg, 0.940 mmol) were combined in MeOH (3 mL) and THF (3 mL) at 50° C. for 3 H. Then sodium borohydride (59 mg, 1.567 mmol) was added at room temperature and allowed to stir for 10 min. The mixture was quenched with water and extracted with ethyl acetate. The organics were dried over MgSO4 and concentrated in vacuo to give methyl 3-((1-(tert-butoxycarbonyl)piperidin-4-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylate (60 mg) which was carried on to the next step. 1H NMR (400 MHz, CD3OD) δ 8.32 (d, 1H, J=5.1 Hz), 7.61-7.62 (m, 2H), 4.07-4.13 (m, 4H), 4.01 (s, 3H), 2.81-2.84 (m, 3H), 1.96-1.98 (m, 2H), 1.45-1.47 (m, 2H), 1.45 (s, 9H). [M+H] found 389.

Workup

  1. customat 50° C.
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organics were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-212a3cd36be94ed9bb3246e2c48cd34e
Source dataset
uspto-grants-2014_07
Patent number
US08785429B2

Reaction notes

Loading…