Thiophene-3-boronic acid → (R)-Methyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

HRID 1054096Notes

Reaction equation

HRID 1054096 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=1.[S:10]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11]1>>[S:10]1[CH:14]=[CH:13][C:12]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=2)=[CH:11]1

Participants

3

Reactant 2

HCID 581760Thiophene-3-boronic acidHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 2764563(R)-Methyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

Procedure

Synthesized using compound 43c (840 mg, 4.52 mmol) and thiophen-3-ylboronic acid (867 g, 6.77 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (8:2) as eluent. Orange solid. Yield: 556 mg, 65%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=7.45 (dd, J=5.0, 2.8 Hz, 1H), 7.72-7.80 (m, 2H), 8.11 (dd, J=2.8, 1.3 Hz, 1H), 8.19 (dd, J=8.2, 2.2 Hz, 1H), 9.06 (dd, J=2.2, 0.9 Hz, 1H), 10.11 (s, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=120.3, 126.3, 126.4, 126.9, 129.6, 136.5, 141.1, 152.6, 158.0, 190.2; (ESI): m/z=190.27 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (8:2) as eluent

Sources & evidence

ORD record
ord-03f30c27881749a1bd4c505bd2c33daf
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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