Acetic Acid → HCID 59238964, compound

HRID 1949116Notes

Reaction equation

HRID 1949116 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9]([O:15][CH2:16][CH2:17][CH2:18][NH2:19])=[C:8]3[NH:20][C:21]4[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][C:26]=4[C:7]3=[CH:6][C:5]2=1.[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([CH:37]=O)=[CH:29]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl>[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([CH2:37][NH:19][CH2:18][CH2:17][CH2:16][O:15][C:9]2[C:8]3[NH:20][C:21]4[C:26](=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=4)[C:7]=3[CH:6]=[C:5]3[C:4]4[CH:3]=[C:2]([Cl:1])[CH:14]=[CH:13][C:12]=4[NH:11][C:10]=23)=[CH:29]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10256Indole-3-CarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59238929HCID 59238929, compound

Product 1

HCID 59238964HCID 59238964, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3-(2,10-dichloro-5,7-dihydroindolo[2,3-b]carbazol-6-yloxy)propan-1-amine (1 equiv) in 1,2-dichloroethane (10 mL/mmol), under an atmosphere of argon, was added 1H-indole-3-carbaldehyde (1 equiv), NaBH(OAc)3 (2 equiv), and then HOAc (2-3 equiv). The resulting mixture was stirred at RT overnight, and then partitioned between dichloromethane and 2 M Na2CO3. The organic layer was washed with brine, dried over Na2SO4, and concentrated. The residue was subjected to chromatography on silica gel, eluting with CH2Cl2/MeOH (10% cNH3.H2O) to the expected product in 50-80% yield. 1H NMR (400 MHz, CD3CN) δ 11.0 (br s, 2H), 9.25 (br s, 1H), 8.31 (s, 1H), 7.99 (d, J=2.4 Hz, 2H), 7.64 (d, J=7.6 Hz, 1H), 7.44 (dt, J=8.4, 0.8 Hz, 1H), 7.21 (d, J=2.4 Hz, 1H), 7.19-7.10 (m, 3H), 7.00 (ddd, J=7.2, 6.8, 0.8 Hz, 1H), 6.93 (d, J=8.4 Hz, 1H), 4.29 (t, J=5.6 Hz, 2H), 4.09 (s, 2H), 3.07 (t, J=6.0 Hz, 2H), 2.00 (pentalet, J=5.8 Hz, 2H).

Workup

  1. custompartitioned between dichloromethane and 2 M Na2CO3
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. washeluting with CH2Cl2/MeOH (10% cNH3.H2O) to the expected product in 50-80% yield

Sources & evidence

ORD record
ord-2f1ea4a113b143dab9c24222b223b856
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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