HCID 25174433, compound → HCID 25174434, compound

HRID 549453Notes

Reaction equation

HRID 549453 reaction equation
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8]([CH3:28])([CH3:27])[C@H:9]2[NH:12][C:13]([C:15]2[NH:16][C:17]3[C:22]([CH:23]=2)=[CH:21][C:20]([N+:24]([O-])=O)=[CH:19][CH:18]=3)=[O:14])=[CH:5][CH:4]=1)#[N:2]>[Pd].C1COCC1.CO>[NH2:24][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:13]([NH:12][C@H:9]1[C:10]3[C:6](=[CH:5][CH:4]=[C:3]([C:1]#[N:2])[CH:11]=3)[CH2:7][C:8]1([CH3:28])[CH3:27])=[O:14])=[CH:23]2

Participants

4

Reactant 1

HCID 25174433HCID 25174433, compound

Product 1

HCID 25174434HCID 25174434, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of (R)—N-(6-cyano-2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-5-nitro-1H-indole-2-carboxamide (200 mg, 0.534 mmol) (prepared as described in Example 8) and 10% Pd/C (80 mg) in 1:1 THF/MeOH (24 mL) was stirred at rt under H2, provided a H2 balloon, for 3 hr. The catalyst was removed by suction filtration, and the filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate (50 mL), washed with brine (20 mL), and dried over anhydrous MgSO4. It was concentrated under vacuum, and the residue was applied to ISCO (12 g silica gel, 40-55% ethyl acetate/hexane) to afford the desired title product (106 mg, 58% yield) as a pale yellow solid. LCMS (M+H)=345.38. 1H NMR (500 MHz, DMSO-d6) δ: 11.1 (s, 1H), 8.33 (d, J=9.3 Hz, 1H), 7.69 (d, J=8.2 Hz, 1H), 7.59 (s, 1H), 7.45 (d, J=7.7 Hz, 1H), 7.14 (d, J=8.8 Hz, 1H), 6.98 (s, 1H), 6.68 (s, 1H), 6.61 (d, J=8.8 Hz, 1H), 5.35 (d, J=9.3 Hz), 4.60 (br. s, 2H), 2.86 (dd, J=23.6, 16.5 Hz, 2H), 1.20 (s, 3H), 0.93 (s, 3H).

Workup

  1. customprovided a H2 balloon
  2. customThe catalyst was removed by suction filtration
  3. concentrationthe filtrate was concentrated under vacuum
  4. additionThe residue was diluted with ethyl acetate (50 mL)
  5. washwashed with brine (20 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationIt was concentrated under vacuum

Sources & evidence

ORD record
ord-ee29b744f7364741a2d5058594006b4b
Source dataset
uspto-grants-2011_05
Patent number
US07943658B2

Reaction notes

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