Phthalimide → HCID 18713524, compound

HRID 279224Notes

Reaction equation

HRID 279224 reaction equation
CO[CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[C:15]([N:17]2[CH2:21][C@@H:20]([CH:22]3[CH2:24][CH2:23]3)[C@H:19]([CH2:25][N:26]3[CH2:31][CH2:30][CH:29]([C:32]4[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=4)[CH2:28][CH2:27]3)[CH2:18]2)=[O:16])[CH:8]=[CH:7]1.C1(=O)[NH:43]C(=O)C2=CC=CC=C12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[NH2:43][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[C:15]([N:17]2[CH2:21][C@@H:20]([CH:22]3[CH2:24][CH2:23]3)[C@H:19]([CH2:25][N:26]3[CH2:27][CH2:28][CH:29]([C:32]4[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=4)[CH2:30][CH2:31]3)[CH2:18]2)=[O:16])[CH:8]=[CH:7]1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 18713516HCID 18713516, compound

Product 1

HCID 18713524HCID 18713524, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1 g (4 mmol) of 7-carboethoxy-N-(3-hydroxypropyl)indole (Example 20, Step 1), 1.23 g (8.4 mmol) of phthalimide, 2.12 g (8 mmol) of triphenylphosphine and 1.28 g (8 mmol) of diethylazodicarboxylate in 15 mL of THF was stirred for 12 h at rt. The reaction mixture was concentrated and partitioned between ether and water that had been made basic. The combined organic fractions were dried over MgSO4, filtered andthe filtrate was concentrated. The residue was purified by chromatography (silica, EtOAc:hexanes, 1:4) to give 1.09 g of the title compound. 1H NMR (CDCl3) δ7.8 (m, 2H), 7.7 (m, 4H), 7.2 (d, 1H), 7.1 (t, 1H), 4.45 (t, 2H), 4.2 (q, 2H), 3.7 (t, 2H), 2.1 (m, 2H), 1.35 (t, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ether and water that
  3. dry with materialThe combined organic fractions were dried over MgSO4
  4. filtrationfiltered andthe filtrate
  5. concentrationwas concentrated
  6. customThe residue was purified by chromatography (silica, EtOAc:hexanes, 1:4)

Sources & evidence

ORD record
ord-b589e30cfa0a435c983a1e91045b9325
Source dataset
uspto-grants-2002_03
Patent number
US06362201B1

Reaction notes

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