3-Nitrophenylboronic Acid → HCID 57502368, compound

HRID 2070890Notes

Reaction equation

HRID 2070890 reaction equation
NC1C=C([C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)C=CC=1.BrC1N2N=C(N)N=C2C=CC=1.[N+](C1C=C(B(O)O)C=CC=1)([O-])=O.C1(Br)C=CC=CC=1.O1C=CC(C2N3N=C(NC4C=CC=CC=4)N=C3C=CC=2)=C1.[N+](C1C=C(C2N3N=C(NC4C=CC=CC=4)N=C3C=CC=2)C=CC=1)([O-])=O.[Cl-].[NH4+]>CO.O1CCCC1.[Zn]>[C:18]1([NH:17][C:15]2[N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][N:13]3[N:14]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

11

Reactant 7

HCID 16773-Nitrophenylboronic AcidHCID 7961BromobenzeneHCID 25517Ammonium ChlorideHCID 252159395-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amineHCID 59276394HCID 59276394, compoundHCID 59276500HCID 59276500, compoundHCID 68589432HCID 68589432, compound

Product 1

HCID 57502368HCID 57502368, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-(3-Aminophenyl)-N-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine. 543-Nitrophenyl)-N-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine was prepared from 5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine, 3-nitro-phenylboronic acid and phenyl bromide according to the procedure described for the synthesis of 5-(furan-3-yl)-N-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine. A mixture of 5-(3-nitrophenyl)-N-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine (170 mg, 0.51 mmol), zinc dust (338 mg, 5.1 mmol), and ammonium chloride (270 mg, 5.1 mmol) in a mixture of methanol and tetrahydrofuran (v/v, 1:1, 8 mL) at room temperature overnight. The reaction mixture was filtered through celite, and the filtrate was concentrated in vacuo to give the crude product, which was washed with ethyl ether to give 5-(3-aminophenyl)-N-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine (79 mg, 51% yield). 1H NMR (400 MHz, METHANOL-d4) δ (ppm) 7.62-7.59 (m, 3H), 7.44 (m, 1H), 7.37 (m, 1H), 7.30-7.24 (m, 4H), 7.08 (m, 1H), 6.89 (m, 2H); MS (ESI): m/z 302.1 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto give the crude product, which

Sources & evidence

ORD record
ord-c400231d3fcb4e5485ea1415acd2fefe
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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