Water → HCID 71523551, compound

HRID 1621004Notes

Reaction equation

HRID 1621004 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C@H:13]([OH:21])[C@@H:14]3[CH2:18][CH2:17][CH2:16][C:15]3=[N:19]O)[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].O>CO.[Ni]>[NH2:19][C@@H:15]1[CH2:16][CH2:17][CH2:18][C@H:14]1[C@H:13]([C:9]1([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:10][CH2:11][CH2:12]1)[OH:21]

Participants

5

Reactant 2

HCID 962WaterHCID 131731659HCID 131731659, compound

Product 1

HCID 71523551HCID 71523551, compoundYield 4.71%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of Example 220B (200 mg, 0.609 mmol) in MeOH (25 mL) was added to Ra—Ni 2800, (water slurry, 500 mg, 9.93 mmol) in a 50 mL pressure bottle and stirred for 16 hours at 30 psi at room temperature, and filtered through a nylon membrane. The filtrate was concentrated and purified using a Waters C8 OBD SunFire 30 mm×75 mm column eluted with acetonitrile/0.1% TFA to afford Example 220C in 4.71% yield. MS (ESI+) M/Z 314 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.58 (d, J=8.3 Hz, 1H), 7.52 (d, J=2.1 Hz, 1H), 7.34 (dd, J=8.4, 2.1 Hz, 1H), 5.85 (d, J=4.3 Hz, 1H), 3.74 (dd, J=9.7, 3.5 Hz, 1H), 3.21-3.29 (m, 1H), 2.06-2.38 (m, 5H), 1.10-1.88 (m, 10H);

Workup

  1. filtrationfiltered through a nylon membrane
  2. concentrationThe filtrate was concentrated
  3. custompurified
  4. washeluted with acetonitrile/0.1% TFA
  5. customto afford Example 220C in 4.71% yield

Sources & evidence

ORD record
ord-e67a177ad41a4150bdcffe14e9698f5e
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

Loading…