HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1972757Generated: November 4, 2026
Dichloromethane → [3-(4-Amino-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzyl]-carbamic acid tert-butyl ester
https://huagongshe.com/reaction/1972757
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | tert-Butyl {[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}carbamate | HCID 2760591 | — |
| Reactant | 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine | HCID 42281383 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | [3-(4-Amino-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzyl]-carbamic acid tert-butyl ester | HCID 71134144 | — |
Reaction Steps
To a solution of [3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-carbamic acid tert-butyl ester (7 g, 21 mmol) in DME (100 mL), 7-bromo-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine (2.5 g, 11.7 mmol), PdCl2(dppf) complexed with CH2Cl2 (850 mg, 1.2 mmol) and 2 N Na2CO3 (12 mL) were added. The mixture was degassed for 20 min and was then heated to 80° C. for 23 hours. After cooling, the mixture was partitioned between EtOAc and H2O, and the organic layer was separated and dried. Biotage® chromatography (50-100% EtOAc) provided the title product as off white solid 2.6 g (76%). 1H NMR (300 MHz, DMSO-d6) δ 7.80-7.50 (m, 6 H), 7.20-7.0 (m, 3 H), 4.80 (s, 2 H), 1.30 (s, 9 H); ES-MS m/z 339 [M+H]+, HPLC RT (min) 2.41.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08431695B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-8e80b09cc79f4c848ef407b99b1d7fc0 |
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| Source note | uspto-grants-2013_04 |
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