Triethylamine → HCID 67412733, compound

HRID 909151Notes

Reaction equation

HRID 909151 reaction equation
B(O)O.[C:4]([O:8][C:9](=[O:20])[NH:10][CH2:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[NH2:19])([CH3:7])([CH3:6])[CH3:5].CC[N:23]([CH2:26][CH3:27])[CH2:24][CH3:25]>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[C:4]([O:8][C:9](=[O:20])[NH:10][CH2:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[NH:19][C:14]1[CH:13]=[C:12]2[C:26](=[CH:27][CH:15]=1)[N:23]([CH2:24][CH:25]1[CH2:6][CH2:4][CH2:5]1)[N:10]=[CH:11]2)([CH3:7])([CH3:5])[CH3:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 61668Boronic AcidHCID 53439196tert-Butyl [(2-amino-5-fluorophenyl)methyl]carbamate

Product 1

HCID 67412733HCID 67412733, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a flask containing boronic acid (0.175 g, 0.76 mmol), amine (6q) (0.22 g, 0.915 mmol), Cu(OAc)2 (0.135 g, 0.76 mmol) and 4 Å sieves (0.2 g) in DCM, Et3N (0.52 mL, 3.7 mmol) was slowly added. The mixture was stirred at room temperature for 3 days. DCM was added to the reaction mixture and filtered. The filtrate was washed with H2O (2×), brine and dried over Na2SO4. After concentration, the residue was purified by chromatography (Sep-Pak; 10 g) with hexane/Et2O (3:1). The fractions containing the product were combined to afford (7q-2) (0.12 g, 37% yield). 1HNMR (400 MHz, CDCl3) δ 7.82 (s, 1H), 7.34 (d, J=8.6 Hz, 1H), 7.24 (br s, 1H), 7.13 (d, J=8.6 Hz, 1H), 6.94-6.84 (m, 3H), 5.02 (br s, NH), 4.35 (d, J=7.8 Hz, 2H), 4.29 (d, j=6.2 Hz, 2H), 2.98-2.85 (m, 1H), 2.10-1.98 (m, 2H), 1.95-1.79 (m, 4H), 1.44 (s, 9H); MS (APCI+) m/z 425 (M+H) was detected.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with H2O (2×), brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentration
  5. customthe residue was purified by chromatography (Sep-Pak; 10 g) with hexane/Et2O (3:1)
  6. additionThe fractions containing the product

Sources & evidence

ORD record
ord-8ca797a6e472433b8618a58d34765636
Source dataset
uspto-grants-2011_09
Patent number
US08017641B2

Reaction notes

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