Cyclopropylboronic acid → HCID 178434211, compound

HRID 1046503Notes

Reaction equation

HRID 1046503 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:5]2[C:15]([CH3:18])=[N:16][NH:17][C:4]=2[CH:3]=1.[CH:19]1(B(O)O)[CH2:21][CH2:20]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:9]1([O:8][C:6]2[C:5]3[C:15]([CH3:18])=[N:16][NH:17][C:4]=3[CH:3]=[C:2]([CH:19]3[CH2:21][CH2:20]3)[N:7]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 2760897Cyclopropylboronic acidHCID 178434291HCID 178434291, compound

Product 1

HCID 178434211HCID 178434211, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

To a microwave tube was added 6-chloro-4-(cyclohexyloxy)-3-methyl-1H-pyrazolo[4,3-c]pyridine (49 mg, 0.18 mmol), cyclopropylboronic acid (80 mg, 0.9 mmol), Pd(dppf)Cl2 (15 mg, 0.018 mmol). The tube was flushed with nitrogen for 2 minutes before adding a 2 M solution of sodium carbonate in water (0.28 mL) and 1,4-dioxane (2 mL). The tube was sealed and irradiated in a microwave at 160° C. for 25 minutes. The reaction mixture was then filtered and concentrated. The crude product was purified by reverse-phase HPLC to give the title compound (8.7 mg, 17%). LC-MS (Method G): m/z=272.1 [M+H]+; 5.44 min. 1H-NMR (400 MHz, DMSO): δ 12.57 (s, 1H), 6.83 (s, 1H), 5.15 (m, 1H), 2.02 (m, 1H), 1.87 (m, 2H), 1.71 (m, 2H), 1.62 (m, 2H), 1.46 (m, 4H), 0.87 (m, 4H).

Workup

  1. customThe tube was flushed with nitrogen for 2 minutes
  2. additionbefore adding a 2 M solution of sodium carbonate in water (0.28 mL) and 1,4-dioxane (2 mL)
  3. customThe tube was sealed
  4. customirradiated in a microwave at 160° C. for 25 minutes
  5. filtrationThe reaction mixture was then filtered
  6. concentrationconcentrated
  7. customThe crude product was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-d2fa023bcd5145dfb86d99cbfee3c5f9
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

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