Trifluoroacetic acid → [5-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-yl]-(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amine

HRID 510010Notes

Reaction equation

HRID 510010 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]([NH2:19])=[N:16][C:17]=3[F:18])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[F:20][C:21]1[CH:22]=[C:23]([CH:29]=O)[C:24]([O:27][CH3:28])=[N:25][CH:26]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]([NH:19][CH2:29][C:23]4[C:24]([O:27][CH3:28])=[N:25][CH:26]=[C:21]([F:20])[CH:22]=4)=[N:16][C:17]=3[F:18])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 226783235-Fluoro-2-methoxynicotinaldehydeHCID 582594945-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-ylamine

Product 1

HCID 58259257[5-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-yl]-(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amine

Conditions

Temperature
80 °C

Procedure

To 5-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-ylamine (173, 1 equivalent) and 5-fluoro-2-methoxy-pyridine-3-carbaldehyde (37, 1 equivalent), triethylsilane (4 equivalents) and trifluoroacetic acid (4 equivalents) are added. The reaction is stirred at 80° C. for several hours, then concentrated under vacuum. The resulting material is taken up in ethyl acetate and extracted with addition of aqueous potassium carbonate. The organic layer is concentrated under vacuum, then triturated with dichloromethane to provide the desired compound.

Workup

  1. concentrationconcentrated under vacuum
  2. extractionextracted with addition of aqueous potassium carbonate
  3. concentrationThe organic layer is concentrated under vacuum
  4. customtriturated with dichloromethane

Sources & evidence

ORD record
ord-71267a7496684dc89201e00a2ee02d12
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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