HCID 11238102, compound → HCID 10161358, compound

HRID 431751Notes

Reaction equation

HRID 431751 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][CH2:20][Cl:21])=[C:11]([NH:22][C:23]([C:25]2[NH:26][C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([O:34][CH3:35])=[C:29]([O:36][CH3:37])[C:28]=3[O:38][CH3:39])=[O:24])[CH:10]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[Cl:21][CH2:20][CH2:19][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([OH:8])=[CH:10][C:11]=1[NH:22][C:23]([C:25]1[NH:26][C:27]2[C:32]([CH:33]=1)=[CH:31][C:30]([O:34][CH3:35])=[C:29]([O:36][CH3:37])[C:28]=2[O:38][CH3:39])=[O:24]

Participants

4

Reactant 1

HCID 11238102HCID 11238102, compound

Product 1

HCID 10161358HCID 10161358, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-[4-benzyloxy-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl chloride (70 mg, 0.13 mmol) in THF (10 mL) was added to a suspension of 10% Pd/C (50 mg) in chilled THF (10 mL) and the suspension was hydrogenated under H2 atmosphere at room temperature overnight. The suspension was filtered over Celite and the filtrate was concentrated in reduced pressure. The residue was crystallized with diethylether to yield 4-(2-chloroethyl)-3-(5,6,7-trimethoxyindole-2-carboxamido)-1-naphthol (54 mg, 91%) as a white solid: mp 212° C. (decomp.); 1H NMR (CDCl3, 500 MHz) δ 9.55 (s, 1H), 8.76 (s, 1H), 8.33 (d, 8.0, 1H), 7.82 (d, 8.5, 1H), 7.78 (brs, 1H), 7.71 (s, 1H), 7.57 (t, 7.0, 1H), 7.48 (t, 7.5, 1H), 7.03 (s, 1H), 6.88 (s, 1H), 4.13 (s, 3H), 4.06 (t, 6.0, 1H), 3.97 (s, 3H), 3.93 (s, 3H), ), 3.61 (t, 6.0, 2H); FABMS (NBA) m/z 455 (M+H+), FABHR (NBA) m/z 454.1290 (M+H+, C24H23ClN2O5 requires 454.1296); IR (neat) νmax 3416, 3193, 3149, 2936, 1621, 1592, 1524, 1435, 1411, 1383, 1328, 1267, 1244, 1197, 1126, 1096, 1054, 852, 821, 758, 743 cm1.

Workup

  1. filtrationThe suspension was filtered over Celite
  2. concentrationthe filtrate was concentrated in reduced pressure
  3. customThe residue was crystallized with diethylether

Sources & evidence

ORD record
ord-60bb8e3a84a44804b341fe86599e5e62
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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