HCID 18761429, compound → HCID 11293471, compound

HRID 431738Notes

Reaction equation

HRID 431738 reaction equation
C(OC([NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][CH2:23][OH:24])=[C:14]([NH:25][C:26]([C:28]2[NH:29][C:30]3[C:35]([CH:36]=2)=[CH:34][C:33]([O:37][CH3:38])=[C:32]([O:39][CH3:40])[C:31]=3[O:41][CH3:42])=[O:27])[CH:13]=1)=O)C1C=CC=CC=1>C1COCC1.[Pd]>[NH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][CH2:23][OH:24])=[C:14]([NH:25][C:26]([C:28]2[NH:29][C:30]3[C:35]([CH:36]=2)=[CH:34][C:33]([O:37][CH3:38])=[C:32]([O:39][CH3:40])[C:31]=3[O:41][CH3:42])=[O:27])[CH:13]=1

Participants

4

Reactant 1

HCID 18761429HCID 18761429, compound

Product 1

HCID 11293471HCID 11293471, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-[4-(N-benzyloxycarbonylamino)-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethanol (0.14 g, 0.25 mmol) in THF (10 mL) was added to a suspension of 10% Pd/C (0.1 g) in chilled THF (10 mL) and the suspension was hydrogenated under H2 atmosphere at room temperature for 3 days. The suspension was filtered over Celite and the filtrate was concentrated in reduced pressure. The residue was crystallized with diisopropylether to yield 2-[4-amino-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethanol (0.083 g, 76%) as a pale yellow solid: mp 172-180° C. (decomp.); 1H NMR (CDCl3, 500 MHz) δ 9.85 (s, 1H), 9.28 (s, 1H), 7.86 (d, 8.5, 1H), 7.86 (d, 8.0, 1H), 7.54 (s, 1H), 7.50 (t, 8.0, 1H), 7.43 (t, 8.5, 1H), 7.03 (d, 2.0, 1H), 6.84 (s, 1H), 4.18 (t, 5.5, 2H), 4.09 (s, 3H), 3.95 (s, 3H), 3.90 (s, 3H), 3.33 (t, 7.0, 2H);); FABMS (NBA) m/z 435 (M+H+), IR (neat) νmax 3291, 2936, 1638, 1595, 1541, 1509, 1464, 1432, 1410, 1305, 1264, 1106, 1047, 996, 909, 833, 757, 731 cm−1.

Workup

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

Sources & evidence

ORD record
ord-b42d9acc778f4915897ed62fbf720ffb
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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