Tin tetrachloride → HCID 178496867, compound

HRID 2174102Notes

Reaction equation

HRID 2174102 reaction equation
[C:1]([C:3]1[CH:45]=[CH:44][C:6]2[N:7](COCC[Si](C)(C)C)[C:8]([C:10]3([C:17]4[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[C:22]5[C:18]=4[CH:19]=[CH:20][N:21]5C(OC(C)(C)C)=O)[CH2:12][CH:11]3[C:13]([O:15][CH3:16])=[O:14])=[N:9][C:5]=2[CH:4]=1)#[N:2].C(C1C=CC2N=C(C3(C4C(OC)=CC(C)=C5C=4C=CN5C(OC(C)(C)C)=O)CC3C(OC)=O)N(COCC[Si](C)(C)C)C=2C=1)#N.Cl[Sn](Cl)(Cl)Cl>ClCCl>[C:1]([C:3]1[CH:45]=[CH:44][C:6]2[NH:7][C:8]([C:10]3([C:17]4[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH3:28])=[C:22]5[C:18]=4[CH:19]=[CH:20][NH:21]5)[CH2:12][CH:11]3[C:13]([O:15][CH3:16])=[O:14])=[N:9][C:5]=2[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 86701740HCID 86701740, compoundHCID 86701741HCID 86701741, compound

Product 1

HCID 178496867HCID 178496867, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (±)-tert-butyl 4-(1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-2-(methoxy carbonyl)cyclopropyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate and (±)-tert-butyl 4-(1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-2-(methoxy carbonyl)cyclopropyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 142-B) (680 mg, 1.078 mmol) in dichloromethane (10.0 mL) at 0° C. was added a 1.0M solution of SnCl4 in dichloromethane (10.78 mL, 10.78 mmol). This mixture was stirred for 30 min at 0° C. followed by 60 min at room temperature. The reaction was partitioned between EtOAc and a saturated aqueous sodium bicarbonate solution. The layers were filtered through Celite® to remove emulsion formed and then the layers were separated. The organic phase was brine washed, dried over Na2SO4 and concentrated in vacuo to afford the crude product. This material was purified using FCC eluting with ethyl acetate/heptane (30-100%) to afford the title compound. MS (ESI+) m/z 401.1 (M+H).

Workup

  1. waitfollowed by 60 min at room temperature
  2. customThe reaction was partitioned between EtOAc
  3. filtrationThe layers were filtered through Celite®
  4. customto remove emulsion
  5. customformed
  6. customthe layers were separated
  7. washwashed
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customto afford the crude product
  11. customThis material was purified
  12. washeluting with ethyl acetate/heptane (30-100%)

Sources & evidence

ORD record
ord-7780722301ed4c06bca3d86f5fad9301
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

Loading…