4-Fluorobenzaldehyde → HCID 16660608, compound

HRID 1429666Notes

Reaction equation

HRID 1429666 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[N:9]=[N:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=2)[CH2:3][CH2:2]1.[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>ClC(Cl)C>[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:1]2[CH2:6][CH2:5][CH:4]([NH:7][C:8]3[N:9]=[N:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=3)[CH2:3][CH2:2]2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 680234-FluorobenzaldehydeHCID 81531DiisopropylethylamineHCID 2724942TriacetoxyborohydrideHCID 59805851HCID 59805851, compound

Product 1

HCID 16660608HCID 16660608, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A suspension of D2 (1.7 g, 5.32 mmol), 4-fluorobenzaldehyde (0.66 g, 5.32 mmol), di-isopropylethylamine (1.37 g, 10.6 mmol) and triacetoxyborohydride on resin (Argonaut Technologies; 2.2 mmol/g; 3 eq.) in dichloroethane (10 ml) was stirred at room temperature for 18 h. After this period, the reaction mixture was filtered and the solvents evaporated in vacuo. The crude product was purified by chromatography (silica; 2%-6% ammonia in methanol (7 M)/dichloromethane) to give E2 (0.79 g, 42%). C17H18F4N4 requires 354; Found 355 (MH+); mp: 163.3-165.3° C. 1H NMR (DMSO-D6) δ 1.48 (q, J=10.8 Hz, 2H), 1.95 (br.d, J=12.5 Hz, 2H), 2.09 (t, J=11.1 Hz, 2H), 2.78 (br.d, J=11.3 Hz, 2H), 3.47 (s, 2H), 3.89 (br.s, 1H), 6.94 (d, J=9.4 Hz, 1H), 7.15 (t, J=8.8 Hz, 2H), 7.34 (dd, J=8.3, 5.7 Hz, 2H), 7.53 (br.d, J=7.3 Hz, 1H), 7.63 (d, J=9.4 Hz, 1H)

Workup

  1. waitAfter this period
  2. filtrationthe reaction mixture was filtered
  3. customthe solvents evaporated in vacuo
  4. customThe crude product was purified by chromatography (silica; 2%-6% ammonia in methanol (7 M)/dichloromethane)

Sources & evidence

ORD record
ord-d8838f7cea1346118231ca412267fbd6
Source dataset
uspto-grants-2015_01
Patent number
US08940743B2

Reaction notes

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