Methanol → 7-[(4-fluorophenyl)methyl]-6,9-dihydroxy-5-methoxy-6H-pyrrolo[3,4-g]quinolin-8-one

HRID 853628Notes

Reaction equation

HRID 853628 reaction equation
[F:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([O:21][Si](C(C)C)(C(C)C)C(C)C)=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([O:32][CH3:33])[C:9]=3[C:8]2=[O:34])=[CH:4][CH:3]=1.CO.[BH4-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([OH:21])=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([O:32][CH3:33])[C:9]=3[CH:8]2[OH:34])=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 58928738HCID 58928738, compound

Product 1

HCID 103834717-[(4-fluorophenyl)methyl]-6,9-dihydroxy-5-methoxy-6H-pyrrolo[3,4-g]quinolin-8-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 13 (0.699 g, 1.38 mmol) in 14 mL of a 1:1 solution of dry MeOH: CH2Cl2 under a N2 atmosphere was added sodium borohydride (NaBH4, 156 mg, 4.13 mmol). The reaction mixture was dried after 5 hours and the residue was loaded onto a silica column. The product was eluted with a 10% EtOAc-Hex to provide the product 20. 1H NMR (300 MHz, CDCl3) δ 1.10 (d, 9H, J=8 Hz), 1.16 (d, 9H, J=7 Hz), 1.52 (septet, 3H, J=8 Hz), 3.72 (d, 1H, J=11 Hz), 4.11 (s, 3H), 4.23 (d, 1H, J=15 Hz), 4.85 (d, 1H, J=15 Hz), 5.79 (d, 11H, J=11 Hz), 6.97 (t, 2H, J=9 Hz), 7.27 (dd, 2H, J=6, 9 Hz), 7.43 (dd, 1H, J=4, 8 Hz), 8.43 (dd, 1H, J=2, 8 Hz), 8.81 (dd, 1H, J=2,4 Hz); 13C NMR (75 MHz, CDCl3) δ 14.8. 18.2,41.3, 61.6, 78.6, 115.3, 115.6, 116.6, 122.3, 126.0, 126.8, 130.1, 130.2, 131.1, 132.8, 143.1, 143.8, 148.3, 162.1 (d, J=244 Hz), 165.2; EI MS (m/z) 511.5 [MH+], 533.4 [M+Na].

Workup

  1. customThe reaction mixture was dried after 5 hours
  2. washThe product was eluted with a 10% EtOAc-Hex

Sources & evidence

ORD record
ord-8135cc116e5b4bf7bfb073ab4212a54c
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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